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Waylon Arnold Jennings (June 15, 1937 – February 13, 2002) was an American country music singer, songwriter, and musician. Jennings began playing at eight. He began performing at twelve, on KVOW radio. Jennings formed a band The Texas Longhorns. Jennings worked as a D.J on KVOW, KDAV and KLLL. In 1958, Buddy Holly arranged Jennings' first recording session, of "Jolie Blon" and "When Sin Stops (Love Begins)". Holly hired Jennings to play bass. Jennings unintentionally missed flying with Holly, The Big Bopper and Ritchie Valens on the flight which they died. Before takeoff, Holly, in jest,... MORE

Waylon Arnold Jennings (June 15, 1937 – February 13, 2002) was an American country music singer, songwriter, and musician. Jennings began playing at eight. He began performing at twelve, on KVOW radio. Jennings formed a band The Texas Longhorns. Jennings worked as a D.J on KVOW, KDAV and KLLL. In 1958, Buddy Holly arranged Jennings' first recording session, of "Jolie Blon" and "When Sin Stops (Love Begins)". Holly hired Jennings to play bass. Jennings unintentionally missed flying with Holly, The Big Bopper and Ritchie Valens on the flight which they died. Before takeoff, Holly, in jest, told Jennings "I hope your ol' bus freezes up", to which Jennings, also in jest, responded with "I hope your ol' plane crashes". These words would haunt Jennings his entire life. He worked as a D.J in Coolidge, Arizona and Phoenix. He formed a rockabilly club band, The Waylors. He recorded for independent label Trend Records, A&M Records before succeeding with RCA Records after achieving creative control of his records. During the 1970s, Jennings joined the Outlaw movement. He released critically acclaimed albums Lonesome, On'ry and Mean and Honky Tonk Heroes, followed by hit albums Dreaming My LESS